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Method for synthesizing benzofuran derivative from phenol and alpha-haloketone

A technology of benzofuran and derivatives is applied in the fields of drug synthesis and chemical product synthesis to achieve the effects of reducing production cost, easy separation and less side reactions

Active Publication Date: 2019-03-26
CHONGQING MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, titanium tetrachloride is used as a dehydrating agent for benzofuran derivatives, and there is no bibliographical information at present.

Method used

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  • Method for synthesizing benzofuran derivative from phenol and alpha-haloketone
  • Method for synthesizing benzofuran derivative from phenol and alpha-haloketone
  • Method for synthesizing benzofuran derivative from phenol and alpha-haloketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the synthesis of benzofuran derivative IIIa

[0029]

[0030] Phenol Ia (2 mmol) and hexafluoroisopropanol (10 mL) were added to a 50 mL two-neck flask equipped with a reflux condenser and under nitrogen protection, and heated to reflux while stirring. After the phenol Ia was completely dissolved, titanium tetrachloride (2mmol) was added, and finally a mixed solution of α-haloketone IIa (2mmol) and hexafluoroisopropanol (2mL) was slowly added dropwise, and the reflux reaction was continued. TLC monitoring. After the reaction was completed, it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and then extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product IIIa as a yellow oil with a yield of 75%.

[0031] 1 H NMR (600MHz, CDCl 3 )δ7.42 (ddd, J=5.7, 3.3,...

Embodiment 2

[0032] Embodiment 2: the synthesis of benzofuran derivative IIIb

[0033]

[0034] In a 50mL two-necked flask under nitrogen protection, add substituted phenol Ib (2mmol) and trifluoroethanol (15mL), stir at room temperature, after the substituted phenol Ib is completely dissolved, add titanium tetrachloride (3mmol), and finally slowly A mixed solution of α-haloketone IIa (3 mmol) and trifluoroethanol (2 mL) was added dropwise to continue the reaction at room temperature, and the reaction process was monitored by TLC. After the reaction was completed, it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and then extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product IIIb as a yellow oil with a yield of 80%.

[0035] 1 H NMR (600MHz, CDCl 3)δ7.30(d, J=8.3Hz, 1H), 7.22(s, 1H)...

Embodiment 3

[0036] Embodiment 3: the synthesis of benzofuran derivative IIIc

[0037]

[0038] In a 50 mL two-neck flask equipped with a reflux condenser and under nitrogen protection, add substituted phenol Ic (2 mmol) and trifluoroethanol (10 mL), and heat to reflux while stirring. After the substituted phenol Ic was completely dissolved, titanium tetrachloride (4mmol) was added, and finally a mixed solution of α-haloketone IIa (2mmol) and trifluoroethanol (2mL) was slowly added dropwise, and the reflux reaction was continued. The reaction process was analyzed by TLC monitor. After the reaction was completed, it was quenched by adding saturated aqueous ammonium chloride solution (10 mL), and then extracted with dichloromethane (3×10 mL). The dichloromethane solution obtained by the mixed extraction was concentrated under reduced pressure, and then separated by silica gel column chromatography to obtain the target product IIIc as a yellow oil with a yield of 75%.

[0039] 1 H NMR (...

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Abstract

The invention provides a method for efficiently preparing a benzofuran derivative by using phenol and alpha-haloketone as raw materials through one-step reaction under the action of titanium tetrachloride. The method comprises the steps that under the protection of inert gas, phenol and perfluoroalkyl alcohol are added and then stirred and heated to reflux, titanium tetrachloride is added, finallya mixed solution of alpha-haloketone and perfluoroalkyl alcohol is dropped in, and after the reaction is completed, the benzofuran derivative is obtained by separation and purification. The synthesismethod can easily obtain raw materials, is low in cost, mild in reaction conditions, simple and easy in operation, few in side reactions, simple in post-treatment and high in product yield, greatly saves the production cost, has good economics benefits, and is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis and chemical product synthesis, and in particular relates to a method for synthesizing benzofuran derivatives by using phenol and alpha-halogenated ketones as raw materials. Background technique [0002] Many natural substances contain benzofuran structural units, and these substances usually have significant biological activity. Therefore, benzofuran derivatives have high synthetic value and have attracted widespread attention. Benzofuran derivatives can be used in various therapeutic fields, such as cancer, central nervous system diseases, inflammation, diabetes, hormonal disorders, kidney diseases, cardiovascular diseases, and have antipyretic, analgesic, antiviral, antifungal and other functions. Currently, more than 30 drugs containing benzofuran structural units have been approved by USFDA. Besides, benzofuran derivatives have also been developed as acaricides, insecticides and herbi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91C07D307/79
CPCC07D307/79C07D307/91
Inventor 唐强罗娟
Owner CHONGQING MEDICAL UNIVERSITY
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